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

HRID 1626383노트

반응식

HRID 1626383 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
110 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-60920c21c31b4508809d18b0c1b05bc0
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785445B2

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