Dimethylformamide → 5-fluoro-1-oxo-2,3-dihydro-1H-indene-4-carbonitrile

HRID 1187035ノート

反応式

HRID 1187035 の反応式
Br[C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:12].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[CH3:42][N:43](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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[C-]#N.[Zn+2].[C-]#N.O>[F:11][C:10]1[CH:9]=[CH:8][C:7]2[C:6](=[O:12])[CH2:5][CH2:4][C:3]=2[C:2]=1[C:42]#[N:43]

参加物

7

反応物 3

HCID 6228DimethylformamideHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 666462974-bromo-5-fluoro-2,3-dihydro-1H-inden-1-one

生成物 1

HCID 552745775-fluoro-1-oxo-2,3-dihydro-1H-indene-4-carbonitrile

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒

反応条件

温度
175 °C

実験手順

To a microwave tube charged with 4-bromo-5-fluoro-2,3-dihydro-1H-inden-1-one (500 mg, 2.2 mmol) and a stir bar was added Pd2(dba)3 (40.0 mg, 0.044 mmol), S-phos (45 mg, 0.11 mmol), zinc cyanide (333 mg, 2.84 mmol), DMF (15 mL), and Water (0.15 mL). The tube was sealed, and purged three times with nitrogen. The reaction was then heated to 175° C. for 3 minutes in a microwave reactor. TLC showed formation of the desired product, along with a small amount of the dimethylaniline adduct. The crude product mixture was diluted with EtOAc, washed with brine, dried over sodium sulfate, adsorbed onto silica, and purified by MPLC. After removal of solvent, 5-fluoro-1-oxo-2,3-dihydro-1H-indene-4-carbonitrile was collected.

後処理

  1. customThe tube was sealed
  2. custompurged three times with nitrogen
  3. additionThe crude product mixture was diluted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. custompurified by MPLC
  7. customAfter removal of solvent, 5-fluoro-1-oxo-2,3-dihydro-1H-indene-4-carbonitrile
  8. customwas collected

出典と根拠

ORDレコード
ord-304d0ade45304a72828aab32bd3ad821
出典データセット
uspto-grants-2014_03
特許番号
US08673920B2

反応ノート

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