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

HRID 1626388ノート

反応式

HRID 1626388 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][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])#[N:2].[OH:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH2:28])=[O:27])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1.C(OCC)(=O)C>[C:26]([C:25]1[CH:29]=[CH:30][C:22]([O:21][C:12]2[CH:11]=[C:10]3[C:5]([CH:6]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:7][CH2:8][O:9]3)=[CH:4][C:3]=2[C:1]#[N:2])=[CH:23][CH:24]=1)(=[O:27])[NH2:28]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 650524-HydroxybenzamideHCID 67288243Tert-butyl 6-cyano-7-fluorochroman-4-carboxylate

生成物 1

HCID 86664391tert-Butyl 7-(4-carbamoylphenoxy)-6-cyanochroman-4-carboxylate収率 83.2%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒2 回

反応条件

温度
120 °C

実験手順

tert-butyl 6-cyano-7-fluorochroman-4-carboxylate (290 mg, 1.05 mmol), 4-hydroxybenzamide (172 mg, 1.25 mmol) and potassium carbonate (347 mg, 2.51 mmol) were diluted with dry NMP (4 mL). The reaction was bubbled with argon for 10 minutes and then heated at 120° C. for 12 hours under a slight argon bubble. The reaction was cooled and loaded directly onto a biotage 40 M cartridge, eluting with 20% ethyl acetate/hexanes to 100% ethyl acetate to yield 1 g of the crude product which was found to contain NMP. The residue was taken up in ethyl acetate and washed twice with water and then brine. The organic layer was dried over magnesium sulfate, filtered and concentrated to provide the desired product (343 mg, 83.2% yield) as a white foam.

後処理

  1. customThe reaction was bubbled with argon for 10 minutes
  2. custombubble
  3. temperatureThe reaction was cooled
  4. washeluting with 20% ethyl acetate/hexanes to 100% ethyl acetate
  5. customto yield 1 g of the crude product which
  6. washwashed twice with water
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-7e69ab0e696b4935b8d04bf867f93f50
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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