Potassium Carbonate → Methyl 7-(4-(tert-butoxycarbonyl)phenoxy)-6-cyanochroman-4-carboxylate

HRID 1021373ノート

反応式

HRID 1021373 の反応式
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1F)[O:9][C:8](C)(C)[CH2:7][CH:6]2[C:16]([O:18][CH3:19])=[O:17])#[N:2].[OH:20][C:21]1[CH:33]=[CH:32][C:24]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CN1CCCC1=O>[C:28]([O:27][C:25]([C:24]1[CH:23]=[CH:22][C:21]([O:20][C:12]2[CH:11]=[C:10]3[C:5]([CH:6]([C:16]([O:18][CH3:19])=[O:17])[CH2:7][CH2:8][O:9]3)=[CH:4][C:3]=2[C:1]#[N:2])=[CH:33][CH:32]=1)=[O:26])([CH3:31])([CH3:29])[CH3:30]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 117640tert-Butyl 4-hydroxybenzoateHCID 67080271Methyl 6-cyano-7-fluoro-2,2-dimethylchroman-4-carboxylate

生成物 1

HCID 67080240Methyl 7-(4-(tert-butoxycarbonyl)phenoxy)-6-cyanochroman-4-carboxylate収率 32.8%

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 (from Example 3, Step E) (700 mg, 2.98 mmol), tert-butyl 4-hydroxybenzoate (578 mg, 2.98 mmol) and K2CO3 (494 mg, 3.57 mmol) were diluted with N-methylpyrrolidone (6 mL) and bubbled with argon for 10 minutes. The reaction was heated to 110° C. and stirred for 5 hours. The reaction was loaded directly onto a Biotage 40M cartridge and eluted with 5% ethyl acetate/hexanes to 100% ethyl acetate to yield the title compound (400 mg, 32.8% yield).

後処理

  1. custombubbled with argon for 10 minutes
  2. washeluted with 5% ethyl acetate/hexanes to 100% ethyl acetate

出典と根拠

ORDレコード
ord-a8dafba262474963b17b054b87ceeec6
出典データセット
uspto-grants-2014_05
特許番号
US08716498B2

反応ノート

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