Water → Carbamic acid, [4-[1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl]-2-thienyl]-, 1,1-dimethylethyl ester (9CI)

HRID 2108747노트

반응식

HRID 2108747 반응식
CC1(C)C(C)(C)OB([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[N:11]([S:18]([C:21]3[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:10]=2)O1.Br[C:30]1[CH:31]=[C:32]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[S:33][CH:34]=1.C(=O)([O-])[O-].[K+].[K+].O>COCCOC.CCOC(C)=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[S:18]([N:11]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:17]2[C:9]([C:30]2[CH:31]=[C:32]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:40])([CH3:39])[CH3:41])[S:33][CH:34]=2)=[CH:10]1)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19]

참가 물질

8

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 497589593-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 56763855tert-Butyl (4-bromothiophen-2-yl)carbamate

생성물 1

HCID 57633069Carbamic acid, [4-[1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl]-2-thienyl]-, 1,1-dimethylethyl ester (9CI)수율 38%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (398 mg, 1 mmol), tert-butyl 4-bromothiophen-2-ylcarbamate (190 mg, 0.68 mmol), potassium carbonate (310 mg, 2.25 mmol), and tetrakis(triphenylphosphine) palladium (0) (20 mg) were combined in 4 mL DME, 1 mL water, and heated to 160° C. in the microwave for 10 minutes, followed by 170° C. for 10 minutes. The reaction mixture was diluted with EtOAc and washed with saturated sodium bicarbonate. The organic layer was filtered through celite and concentrated to an oil which was purified by column chromatography on silica (15 to 60% EtOAc/hexanes) to give the product as a brown foam, 0.12 g, 0.26 mmol, 38% yield. MH+ 470.1.

후처리

  1. washwashed with saturated sodium bicarbonate
  2. filtrationThe organic layer was filtered through celite
  3. concentrationconcentrated to an oil which
  4. customwas purified by column chromatography on silica (15 to 60% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-c4759cfd080a4d46afb88938193b4649
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514448B2

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