Triethylamine → HCID 58266751、化合物

HRID 1888373ノート

反応式

HRID 1888373 の反応式
[Br:1][C:2]1[CH:17]=[N:16][C:5]2[NH:6][C:7]3[CH:12]=[N:11][C:10]([C:13]([NH2:15])=O)=[CH:9][C:8]=3[C:4]=2[CH:3]=1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[Br:1][C:2]1[CH:17]=[N:16][C:5]2[NH:6][C:7]3[CH:12]=[N:11][C:10]([C:13]#[N:15])=[CH:9][C:8]=3[C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 582667993-Bromo-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carboxylic acid amide

生成物 1

HCID 58266751HCID 58266751、化合物収率 49%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a cooled solution (0° C.) of a mixture of 3-bromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carboxylic acid amide (5.0 g, 17.2 mmol) and triethylamine (24.0 mL, 172 mmol) in THF (200 mL) was slowly added trifluoroacetic anhydride (12.0 mL, 86 mmol). Upon complete addition, the reaction mixture was allowed to warm to ambient temperature and the stirring was continued for an additional 4 h. After this time, the solvent was removed in vacuo and the resultant residue was loaded onto H-MN. The residue was then purified by flash chromatography (silica, 330 g column, ISCO, 0-100% ethyl acetate in hexane) to afford the title compound as a pale brown solid (2.30 g, 49%). 1H NMR (DMSO-D6, 300 MHz): 13.05 (s, 1H), 9.08-9.04 (m, 2H), 8.91 (d, J=1.1 Hz, 1H), 8.79 (d, J=2.3 Hz, 1H). LCMS (Method B): RT=2.98 min, M+H+=271, 273.

後処理

  1. additionUpon complete addition
  2. customAfter this time, the solvent was removed in vacuo
  3. customThe residue was then purified by flash chromatography (silica, 330 g column, ISCO, 0-100% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-e6e9ea70e8a84be48196d9fd339d8dfa
出典データセット
uspto-grants-2013_08
特許番号
US08501765B2

反応ノート

読み込み中…