Potassium Phosphate, Tribasic → 4-(2-Fluoro-4-trimethylsilanyl-phenylamino)-benzo[d]isothiazole-5-carboxylic acid tert-butyl ester

HRID 79028노트

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HRID 79028 반응식
[F:1][C:2]1[CH:7]=[C:6]([Si:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[NH2:12].[C:13]([O:17][C:18]([C:20]1[CH:21]=[CH:22][C:23]2[S:27][N:26]=[CH:25][C:24]=2[C:28]=1Br)=[O:19])([CH3:16])([CH3:15])[CH3:14].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:13]([O:17][C:18]([C:20]1[CH:21]=[CH:22][C:23]2[S:27][N:26]=[CH:25][C:24]=2[C:28]=1[NH:12][C:3]1[CH:4]=[CH:5][C:6]([Si:8]([CH3:9])([CH3:11])[CH3:10])=[CH:7][C:2]=1[F:1])=[O:19])([CH3:16])([CH3:14])[CH3:15]

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 58374343Tert-butyl 4-bromobenzo[d]isothiazole-5-carboxylateHCID 595965992-Fluoro-4-(trimethylsilyl)aniline

생성물 1

HCID 670835784-(2-Fluoro-4-trimethylsilanyl-phenylamino)-benzo[d]isothiazole-5-carboxylic acid tert-butyl ester수율 78.1%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

A solution of 2-fluoro-4-trimethylsilanyl-phenylamine (340 mg, 1.43 mmol), 4-bromo-benzo[d]isothiazole-5-carboxylic acid tert-butyl ester (449 mg, 1.43 mmol), Pd2 dba3 (65 mg, 0.07 mmol), Xantphos (83 mg, 0.14 mmol) and potassium phosphate tribasic (455 mg, 2.14 mmol) in toluene (5 mL) was degassed and then the reaction mixture heated at 90° C. for 18 hours. The cooled reaction mixture was diluted with ethyl acetate, filtered through Celite®, and the filtrate concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si—PPC, gradient 2.5 to 5% diethyl ether in pentane) to give the title compound as a dark oil (465 mg, 78%). LCMS (Method B): RT=5.76 min, [M+H]+=417.

후처리

  1. customThe cooled reaction mixture
  2. filtrationfiltered through Celite®
  3. concentrationthe filtrate concentrated in vacuo

출처 및 근거

ORD 기록
ord-08870ac8b2754831847f6c1f3cdc3533
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841462B2

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