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Potassium Phosphate, Tribasic → (3,5-difluoro(4-pyridyl))-N-[5-(2,2-difluoro-6-methylbenzo[d]1,3-dioxolen-5-yl)(1,3-thiazol-2-yl)]carboxamide

HRID 1524248
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HRID 1524248 반응식
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:17])[C:7]=1[C:8]([NH:10][C:11]1[S:12][C:13](Br)=[CH:14][N:15]=1)=[O:9].[F:18][C:19]1([F:38])[O:23][C:22]2[CH:24]=[C:25]([CH3:37])[C:26](B3OC(C)(C)C(C)(C)O3)=[CH:27][C:21]=2[O:20]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(#N)C.O1CCOCC1.O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:17])[C:7]=1[C:8]([NH:10][C:11]1[S:12][C:13]([C:26]2[C:25]([CH3:37])=[CH:24][C:22]3[O:23][C:19]([F:18])([F:38])[O:20][C:21]=3[CH:27]=2)=[CH:14][N:15]=1)=[O:9]
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참가 물질

8

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 584872352-(2,2-Difluoro-6-methylbenzo[d][1,3]dioxol-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 88576617(3,5-difluoro(4-pyridyl))-N-(5-bromo(1,3-thiazol-2-yl))carboxamide

생성물 1

HCID 56848403(3,5-difluoro(4-pyridyl))-N-[5-(2,2-difluoro-6-methylbenzo[d]1,3-dioxolen-5-yl)(1,3-thiazol-2-yl)]carboxamide수율 40.8%

시약·촉매·용매 4

HCID 962
Water
용매
HCID 6342Acetonitrile용매
HCID 8857Ethyl Acetate용매
HCID 312751,4-Dioxane용매

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온도
85 °C

실험 절차

Argon was bubbled through a mixture of (3,5-difluoro(4-pyridyl))-N-(5-bromo(1,3-thiazol-2-yl))carboxamide (148) (32 mg, 0.1 mmol), 2-(2,2-difluoro-6-methylbenzo[d][1,3]dioxol-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (45 mg, 0.15 mmol), bis(ditertbutyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (11 mg, 10% mol) and K3PO4 (32 mg) in 1 mL ACN, 1 mL dioxane, 0.5 ml H2O. The reaction mixture was heated at 85° C. for 4 h. After cooling to room temperature, the reaction mixture was taken up in ethyl acetate, washed with aqueous NaHCO3 and brine. The organic phase was dried (Na2SO4), concentrated and then subjected to prep HPLC chromatography to give (3,5-difluoro(4-pyridyl))-N-[5-(2,2-difluoro-6-methylbenzo[d]1,3-dioxolen-5-yl)(1,3-thiazol-2-yl)]carboxamide (149) (16.8 mg, yield: 40.8%, purity>95%). LC-MS: calcd. for C17H9F4N3O3S: 412 (M+1).

후처리

  1. temperatureAfter cooling to room temperature
  2. washwashed with aqueous NaHCO3 and brine
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0edfcf7ded654216b46f6dd2bdb09151
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09079891B2

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