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Potassium Carbonate → (S)-tert-butyl 7-((3-methyloxetan-3-yl)ethynyl)-3-(6-methylpyridin-3-yl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-thiazole]-2'-ylcarbamate

HRID 335942
ノート
印刷プレビュー

反応式

HRID 335942 の反応式
Br[C:2]1[CH:3]=[C:4]2[C@:15]3([CH2:19][S:18][C:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[N:16]3)[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:28]#[C:29][C:30]4([CH3:34])[CH2:33][O:32][CH2:31]4)[CH:13]=3)[O:8][C:5]2=[N:6][CH:7]=1.[CH3:35][C:36]1[N:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1.C(=O)([O-])[O-].[K+].[K+]>>[CH3:34][C:30]1([C:29]#[C:28][C:12]2[CH:13]=[C:14]3[C@@:15]4([CH2:19][S:18][C:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[N:16]4)[C:4]4[C:5](=[N:6][CH:7]=[C:2]([C:39]5[CH:40]=[N:41][C:36]([CH3:35])=[CH:37][CH:38]=5)[CH:3]=4)[O:8][C:9]3=[CH:10][CH:11]=2)[CH2:31][O:32][CH2:33]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 3

HCID 11430Potassium CarbonateHCID 27630812-Methylpyridine-5-boronic acidHCID 67437931(S)-tert-butyl 3-bromo-7-((3-methyloxetan-3-yl)ethynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-thiazole]-2'-ylcarbamate

生成物 1

HCID 67436896(S)-tert-butyl 7-((3-methyloxetan-3-yl)ethynyl)-3-(6-methylpyridin-3-yl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-thiazole]-2'-ylcarbamate収率 49%

反応条件

温度
80 °C

実験手順

A vial was charged with (S)-tert-butyl 3-bromo-7-((3-methyloxetan-3-yl)ethynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-thiazole]-2′-ylcarbamate (0.054 g, 0.10 mmol), 6-methylpyridin-3-ylboronic acid (0.041 g, 0.30 mmol), potassium carbonate (0.069 g, 0.50 mmol), and Pd(AmPhos)2Cl2 (7.05 mg, 9.95 μmol). The vial was flushed with Ar (g), then dioxane (0.66 mL) and water (0.33 mL) were added in sequence. The vial was sealed and heated at 80° C. for 16 h. The reaction was diluted with EtOAc and washed with water. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography on silica gel (0-75% EtOAc:Hex) to afford (S)-tert-butyl 7-((3-methyloxetan-3-yl)ethynyl)-3-(6-methylpyridin-3-yl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-thiazole]-2′-ylcarbamate (0.027 g, 0.049 mmol, 48.9% yield) as a white solid. MS m/z=555.3 [M+H]+. Calculated for C31H30N4O4S: 554.20.

後処理

  1. customThe vial was flushed with Ar (g)
  2. additiondioxane (0.66 mL) and water (0.33 mL) were added in sequence
  3. customThe vial was sealed
  4. additionThe reaction was diluted with EtOAc
  5. washwashed with water
  6. extractionThe aqueous layer was extracted with EtOAc
  7. dry with materialthe combined organic layers were dried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe material was purified via column chromatography on silica gel (0-75% EtOAc:Hex)

出典と根拠

ORDレコード
ord-1cc87b8b00374c05859c26a108bff38e
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08883782B2

反応ノート

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