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

HRID 2108747ノート

反応式

HRID 2108747 の反応式
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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c4759cfd080a4d46afb88938193b4649
出典データセット
uspto-grants-2009_04
特許番号
US07514448B2

反応ノート

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