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

HRID 1626388노트

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HRID 1626388 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][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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매2회

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온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7e69ab0e696b4935b8d04bf867f93f50
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785445B2

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