Cesium carbonate → HCID 71209420, 화합물

HRID 1912535

반응식

HRID 1912535 반응식
[CH3:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[C:3]=1[C:18]([O:20][CH3:21])=[O:19].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Br)=[C:31]([F:37])[CH:30]=1.[NH4+].[Cl-]>CN(C)C=O.CCOC(C)=O>[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][N:8]2[C:6]3=[N:7][C:2]([CH3:1])=[C:3]([C:18]([O:20][CH3:21])=[O:19])[C:4]([C:11]4[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=4)=[C:5]3[CH:10]=[CH:9]2)=[C:31]([F:37])[CH:30]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 27365514-Chloro-2-fluorobenzyl bromideHCID 71209360methyl 6-methyl-4-(p-tolyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

생성물 1

HCID 71209420HCID 71209420, 화합물수율 55.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
65 °C

실험 절차

Methyl 6-methyl-4-(p-tolyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (300 mg, 1.070 mmol) (example 1 step F) was dissolved in N,N-dimethylformamide (DMF) (10.700 ml). Cesium carbonate (418 mg, 1.284 mmol) and 4-chloro-2-fluorobenzyl bromide (263 mg, 1.177 mmol) were added to the solution. The reaction was set to stir at 65° C. overnight. The reaction was worked up by adding a saturated aqueous solution of NH4Cl followed by EtOAc. The layers were separated and the organic fraction was washed with water and brine. The reaction was dried over sodium sulfate and concentrated. The crude oil was passed on silica (0-60% AcOEt/Hex) and methyl 1-(4-chloro-2-fluorobenzyl)-6-methyl-4-(p-tolyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (250 mg, 0.591 mmol, 55.2% yield) was recovered as a yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ=7.46-7.39 (m, J=8.0 Hz, 2 H), 7.35-7.26 (m, J=7.9 Hz, 2 H), 7.18 (d, J=3.5 Hz, 1 H), 7.15-7.08 (m, 2 H), 7.07-7.00 (m, 1 H), 6.43 (d, J=3.5 Hz, 1 H), 5.53 (s, 2 H), 3.67 (s, 3 H), 2.75 (s, 3 H), 2.44 (s, 3 H) LCMS (m/z) ES+=423.2 (M+1).

후처리

  1. customThe layers were separated
  2. washthe organic fraction was washed with water and brine
  3. dry with materialThe reaction was dried over sodium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-eaca9f2ab47445c6bc3b77e79a5c3fbd
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609653B2

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