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

HRID 2239981ノート

反応式

HRID 2239981 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

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

反応条件

温度
160 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3c4cb123ce06497496bb6c6ecd9d1b8b
出典データセット
uspto-grants-2010_05
特許番号
US07723345B2

反応ノート

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