Lithium Chloride → HCID 86700382、化合物

HRID 879558ノート

反応式

HRID 879558 の反応式
Br[C:2]1[N:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[N:13]([CH3:17])[N:12]=[CH:11]3)[N:5]([CH3:7])[CH:6]=1.[Li+].[Cl-].Br[C:21]1[S:22][C:23]2[C:29]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)=[C:28]([C@H:37]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[C:38]([O:40][CH2:41][CH3:42])=[O:39])[C:27]([CH3:48])=[CH:26][C:24]=2[N:25]=1>O1CCOCC1.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:44]([O:43][C@@H:37]([C:28]1[C:27]([CH3:48])=[CH:26][C:24]2[N:25]=[C:21]([C:2]3[N:3]=[C:4]([C:8]4[CH:9]=[C:10]5[C:14](=[CH:15][CH:16]=4)[N:13]([CH3:17])[N:12]=[CH:11]5)[N:5]([CH3:7])[CH:6]=3)[S:22][C:23]=2[C:29]=1[C:30]1[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=1)[C:38]([O:40][CH2:41][CH3:42])=[O:39])([CH3:45])([CH3:46])[CH3:47]

参加物

8

反応物 3

HCID 433294Lithium ChlorideHCID 86700141(S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetateHCID 86700381HCID 86700381、化合物

生成物 1

HCID 86700382HCID 86700382、化合物

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 178418476HCID 178418476、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
90 °C

実験手順

In a 10 mL reaction vial, 5-(4-bromo-1-methyl-1H-imidazol-2-yl)-1-methyl-1H-indazole (50 mg, 0.172 mmol) was dissolved in dioxane (3 mL) at rt. The solution was bubbled with argon for 5 min. Then Sn2(n-Bu)6 (0.136 mL, 0.259 mmol), LiCl (60 mg, 1.4 mmol), Pd(PPh3)2Cl2 (24 mg, 0.034 mmol) and Pd(PPh3)4 (40 mg, 0.0344 mmol) were added sequentially. The resulting reaction mixture was sealed and heated to 90° C. in oil bath. To this mixture, a solution of (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (128 mg, 0.259 mmol) in dioxane (1.5 mmol) was added slowly through syringe pump over 1.5 h. The resulting reaction mixture was stirred at 100° C. in oil bath for 16 h. The reaction was then diluted with EtOAc (20 mL) and filtered to remove solid. The filtrate was concentrated and purified on silica gel column with 0-20% EtOAc/Hex to afford product. LCMS-ESI+: calc'd for: C34H34ClN5O3S: 628.2, 629.2, 630.2 (M+H+); found: 628.1, 629.1, 630.1 (M+H+)

後処理

  1. customIn a 10 mL reaction vial
  2. customThe solution was bubbled with argon for 5 min
  3. customThe resulting reaction mixture
  4. customwas sealed
  5. customThe resulting reaction mixture
  6. filtrationfiltered
  7. customto remove solid
  8. concentrationThe filtrate was concentrated
  9. custompurified on silica gel column with 0-20% EtOAc/Hex
  10. customto afford product

出典と根拠

ORDレコード
ord-b36109c56bd5434f89dc63ff7443df99
出典データセット
uspto-grants-2015_03
特許番号
US08987250B2

反応ノート

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