Triethylamine → 8-Fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-9-vinyl-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene

HRID 1530728노트

반응식

HRID 1530728 반응식
Br[C:2]1[C:3]([F:25])=[CH:4][C:5]2[O:14][CH2:13][CH2:12][N:11]3[C:7](=[N:8][C:9]([C:15]4[N:16]([CH:21]([CH3:23])[CH3:22])[N:17]=[C:18]([CH3:20])[N:19]=4)=[CH:10]3)[C:6]=2[CH:24]=1.[CH:26]([B-](F)(F)F)=[CH2:27].[K+].C(N(CC)CC)C>C(O)CC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:25][C:3]1[C:2]([CH:26]=[CH2:27])=[CH:24][C:6]2[C:7]3[N:11]([CH2:12][CH2:13][O:14][C:5]=2[CH:4]=1)[CH:10]=[C:9]([C:15]1[N:16]([CH:21]([CH3:23])[CH3:22])[N:17]=[C:18]([CH3:20])[N:19]=1)[N:8]=3

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 6831287410-Bromo-9-fluoro-2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

생성물 1

HCID 683126378-Fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-9-vinyl-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene수율 88%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 10311-Propanol용매

실험 절차

A degassed solution of 9-bromo-8-fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene from Example 8 (5.0 g, 12.31 mmol), potassium vinyltrifluoroborate (2.47 g, 18.46 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (1.01 g, 1.23 mmol) and triethylamine (8.58 mL, 61.55 mmol) in nPrOH (50 mL) was heated to 100° C. for 2 h. The reaction mixture was concentrated in vacuo; the residue was taken up in EtOAc and filtered through celite. Organics were washed with water and brine, dried (Na2SO4) and concentrated in vacuo to give the title compound (3.82 g, 10.81 mmol, 88%) as a peach solid. The product was taken on without further purification. LCMS (Method J): RT=3.35 min, [M+H]+ =354.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. filtrationfiltered through celite
  3. washOrganics were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-66014584fb64468b9508bf2a14bafc0d
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090628B2

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