Cyanogen Bromide → 2-[Bis(cyclopropylmethyl)amino]-6-fluoropyridine-3-carbaldehyde

HRID 1911794노트

반응식

HRID 1911794 반응식
FC(F)(F)C1C=C(C=C(C(F)(F)F)C=1)CN[CH2:8][C:9]1[C:10]([N:16]([CH2:21][CH:22]2[CH2:24][CH2:23]2)[CH2:17][CH:18]2[CH2:20][CH2:19]2)=[N:11][C:12]([F:15])=[CH:13][CH:14]=1.C(=O)(O)[O-:35].[Na+].N#CBr>CO>[CH:18]1([CH2:17][N:16]([CH2:21][CH:22]2[CH2:24][CH2:23]2)[C:10]2[C:9]([CH:8]=[O:35])=[CH:14][CH:13]=[C:12]([F:15])[N:11]=2)[CH2:20][CH2:19]1

참가 물질

5

반응물 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 58795818HCID 58795818, 화합물

생성물 1

HCID 587957962-[Bis(cyclopropylmethyl)amino]-6-fluoropyridine-3-carbaldehyde

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To {3-[(3,5-bis-trifluoromethyl-benzylamino)-methyl]-6-fluoro-pyridin-2-yl}-bis-cyclopropylmethyl-amine (302 mg, 0.64 mmol) stirred in methanol (10 mL) was added sodium bicarbonate (139.6 mg, 1.24 mmol). After stirring at room temperature for about 15 minutes, cyanogen bromide (237.5 mg, 1.12 mmol) was added and the solution was allowed to stir at room temperature for about 4 hours. The solution was extracted with ethyl acetate (2×15 mL). The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered, and then concentrated under vacuum to give the title compound as an orange oily product (284 mg, yield: 87%) and was used as is without purification.

후처리

  1. stirringto stir at room temperature for about 4 hours
  2. extractionThe solution was extracted with ethyl acetate (2×15 mL)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-de21bae025c14f52b030d5abeeff2035
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604055B2

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