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

HRID 1524249
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HRID 1524249 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]([NH:11][C:12]1[S:13][C:14](Br)=[CH:15][N:16]=1)=[O:10].[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:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]([NH:11][C:12]1[S:13][C:14]([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:15][N:16]=1)=[O:10]
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참가 물질

8

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HCID 62657Potassium Phosphate, TribasicHCID 54918070N-(5-bromo(1,3-thiazol-2-yl))(2,6-difluorophenyl)carboxamideHCID 584872352-(2,2-Difluoro-6-methylbenzo[d][1,3]dioxol-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

생성물 1

HCID 56848444(2,6-difluorophenyl)-N-[5-(2,2-difluoro-6-methylbenzo[d]1,3-dioxolen-5-yl)(1,3-thiazol-2-yl)]carboxamide수율 9%

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 (2,6-difluorophenyl)-N-(5-bromo(1,3-thiazol-2-yl))carboxamide (152) (64 mg, 0.2 mmol), 2-(2,2-difluoro-6-methylbenzo[d][1,3]dioxol-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (489 mg, 0.3 mmol), bis(ditertbutyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (21 mg, 10% mol) and K3PO4 (64 mg) in 1 mL ACN, 1 mL dioxane, 0.5 ml H2O. The reaction mixture was heated at 85° C. for 7 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 over (Na2SO4), concentrated and then subjected to prep HPLC chromatography to give (2,6-difluorophenyl)-N-[5-(2,2-difluoro-6-methylbenzo[d]1,3-dioxolen-5-yl)(1,3-thiazol-2-yl)]carboxamide (153) (7.4 mg, yield: 9%, purity>95%) as white solid. LC-MS: calcd. for C18H10F4N2O3S: 411 (M+1).

후처리

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

출처 및 근거

ORD 기록
ord-0bfb80ed5abe41fc8e28c96793a0f59a
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09079891B2

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