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

HRID 1911794ノート

反応式

HRID 1911794 の反応式
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

参加物

5

反応物 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 58795818HCID 58795818、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-de21bae025c14f52b030d5abeeff2035
出典データセット
uspto-grants-2013_12
特許番号
US08604055B2

反応ノート

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