Potassium Carbonate → Methyl 7-(4-carbamoylphenoxy)-6-cyanochroman-4-carboxylate

HRID 1626383ノート

反応式

HRID 1626383 の反応式
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1F)[O:9][CH2:8][CH2:7][CH:6]2[C:14]([O:16][CH3:17])=[O:15])#[N:2].[OH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH2:25])=[O:24])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[C:23]([C:22]1[CH:26]=[CH:27][C:19]([O:18][C:12]2[CH:11]=[C:10]3[C:5]([CH:6]([C:14]([O:16][CH3:17])=[O:15])[CH2:7][CH2:8][O:9]3)=[CH:4][C:3]=2[C:1]#[N:2])=[CH:20][CH:21]=1)(=[O:24])[NH2:25]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 650524-HydroxybenzamideHCID 67080208Methyl 6-cyano-7-fluorochroman-4-carboxylate

生成物 1

HCID 46929190Methyl 7-(4-carbamoylphenoxy)-6-cyanochroman-4-carboxylate収率 22.3%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
110 °C

実験手順

Methyl 6-cyano-7-fluorochroman-4-carboxylate (300 mg, 1.28 mmol), 4-hydroxybenzamide (227 mg, 1.66 mmol) and potassium carbonate (423 mg, 3.06 mmol) were diluted with dry NMP (4 mL). The reaction was bubbled with argon for 10 minutes and then heated at 110° C. for 12 hours. The reaction was cooled and loaded directly onto a biotage 40M cartridge (silica gel), eluting with 5% ethyl acetate/hexanes to 100% ethyl acetate to yield methyl 7-(4-carbamoylphenoxy)-6-cyanochroman-4-carboxylate (100 mg, 22.3% yield).

後処理

  1. customThe reaction was bubbled with argon for 10 minutes
  2. temperatureThe reaction was cooled
  3. washeluting with 5% ethyl acetate/hexanes to 100% ethyl acetate

出典と根拠

ORDレコード
ord-60920c21c31b4508809d18b0c1b05bc0
出典データセット
uspto-grants-2014_07
特許番号
US08785445B2

反応ノート

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