Dimethylformamide → Tert-butyl 2-(diphenylmethyleneamino)-3-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate

HRID 469892노트

반응식

HRID 469892 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([N:17]=[C:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[C:4]([F:31])[CH:3]=1.[CH:32]1(P(C2CCCCC2)C2CCCCC2)[CH2:37]CCC[CH2:33]1.[O:51]1CCO[BH:52]1.[CH3:56][C:57]([O-:59])=O.[K+].[CH3:61]N(C=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.[Pd]>[C:19]1([C:18](=[N:17][CH:9]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([B:52]3[O:51][C:32]([CH3:37])([CH3:33])[C:57]([CH3:56])([CH3:61])[O:59]3)=[CH:3][C:4]=2[F:31])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 75806TricyclohexylphosphineHCID 517044Potassium AcetateHCID 5326306InChI=1/C2H5BO2/c1-2-5-3-4-1/h3H,1-2HHCID 87090002Tert-butyl 3-(4-bromo-2-fluorophenyl)-2-(diphenylmethylene-amino)propanoate

생성물 1

HCID 87090021Tert-butyl 2-(diphenylmethyleneamino)-3-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate

시약·촉매·용매 1

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매

반응 조건

온도
160 °C

실험 절차

An Emrys process vial (20 ml) for microwave was charged with tert-butyl 3-(4-bromo-2-fluorophenyl)-2-(diphenylmethylene-amino)propanoate (600 mg, 1.24 mmol), Pd(dba)2 (71 mg, 0.124 mmol), PCy3 (35 mg, 0.124 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane (346 mg, 1.1 eq. 1.36 mmol) and KOAc (182 mg, 1.5 eq., 1.86 mmol) 20 ml of DMF. The reaction vessel was sealed and heated to 160° C. for 20 minutes by microwave. After cooling, the reaction mixture was evaporated to dryness under reduced pressure. The residue was dissolved in H2O (30 ml), extracted with EtOAc (2×40 ml), and purified with Prep-LC to give 220 mg of tert-butyl 2-(diphenylmethyleneamino)-3-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate.

후처리

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated to dryness under reduced pressure
  4. dissolutionThe residue was dissolved in H2O (30 ml)
  5. extractionextracted with EtOAc (2×40 ml)
  6. custompurified with Prep-LC

출처 및 근거

ORD 기록
ord-8edbaad356f64eb99f28bc596657e57f
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629156B2

반응 노트

불러오는 중…