Triethylamine → 5-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]pyrazine-2-carbonitrile

HRID 729453ノート

反応式

HRID 729453 の反応式
[Br:1][C:2]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:12]=[CH:13][C:14]([C:17]([NH2:19])=O)=[N:15][CH:16]=2)[CH2:7][CH2:6]1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>>[Br:1][C:2]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:12]=[CH:13][C:14]([C:17]#[N:19])=[N:15][CH:16]=2)[CH2:7][CH2:6]1

参加物

4

反応物 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 690622895-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]pyrazine-2-carboxamide

生成物 1

HCID 688192205-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]pyrazine-2-carbonitrile

実験手順

To a suspension of 5-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyrazine-2-carboxamide from Step 4 (1.65 g, 4.17 mmol) in TBF (50 mL) at 0° C. was added triethylamine (1.45 mL, 10.5 mmol) followed by trifluoroacetic anhydride (0.885 mL, 6.26 mmol). After a period of 10 min at 0° C., the reaction mixture was raised gradually to room temperature. The mixture was then partitioned between ethyl acetate and aqueous sodium bicarbonate. The organic phase was separated, dried over sodium sulfate and evaporated. The crude mixture was purified by flash chromatography (35% ethyl acetate in hexane) to provide the title compound.

後処理

  1. customThe mixture was then partitioned between ethyl acetate and aqueous sodium bicarbonate
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe crude mixture was purified by flash chromatography (35% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-928bd42788174a00a6b2e0288675f414
出典データセット
uspto-grants-2009_09
特許番号
US07582633B2

反応ノート

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