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 1530728ノート

反応式

HRID 1530728 の反応式
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

参加物

6

反応物 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

生成物 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]azulene収率 88%

試薬・触媒・溶媒 2

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-66014584fb64468b9508bf2a14bafc0d
出典データセット
uspto-grants-2015_07
特許番号
US09090628B2

反応ノート

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