Ammonium Chloride → HCID 21106569、化合物

HRID 1783669ノート

反応式

HRID 1783669 の反応式
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12]([Br:16])=[N:11][N:10]([CH:17]([CH3:19])[CH3:18])[C:9]2=[O:20])=O)C.[Li+].[BH4-].[NH4+].[Cl-]>C1COCC1>[Br:16][C:12]1[C:13]2[C:8](=[CH:7][C:6]([CH2:4][OH:3])=[CH:15][CH:14]=2)[C:9](=[O:20])[N:10]([CH:17]([CH3:19])[CH3:18])[N:11]=1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydride2 回HCID 68898772Bromo-3-isopropyl-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid ethyl ester

生成物 1

HCID 21106569HCID 21106569、化合物収率 44.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

Bromo-3-isopropyl-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid ethyl ester (2.3 g, 6.8 mmol) was suspended in THF (50 ml) and cooled to 0° C. To the suspension was added LiBH4 (5.1 ml of a 2M solution in THF, 10.2 mmol) dropwise, the suspension was allowed to warm to RT and stirred for 24 hours. After this time, LC-MS showed 50% starting material remained. To this was added LiBH4 (1.7 ml of a 2M solution in THF, 3.4 mmol) and the reaction mixture was stirred for a further 3 hours. The reaction was cooled to 0° C., saturated NH4Cl (40 ml) was added and the reaction mixture was then partitioned between water (50 ml) and DCM (150 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated under vacuum. The resulting residue was then purified by flash column chromatography (elution: 50% toluene, 30% EtOAc, 20% DCM) to give the title compound (0.9 g, 43% yield) as a white solid. 1H-NMR: (400 MHz, D6-DMSO), 8.28 (1H, s), 7.96 (1H, d), 7.88 (1 H, d), 5.64 (1H, t), 5.31-5.18 (1H, m), 4.78 (2H, d), 1.35 (6H, d); MS (ESI+)=(M+H)+ 297 & 299

後処理

  1. temperatureto warm to RT
  2. stirringwas stirred for a further 3 hours
  3. temperatureThe reaction was cooled to 0° C.
  4. customthe reaction mixture was then partitioned between water (50 ml) and DCM (150 ml)
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe resulting residue was then purified by flash column chromatography (elution: 50% toluene, 30% EtOAc, 20% DCM)

出典と根拠

ORDレコード
ord-866127e293914165a8ab8b3a807a9b0f
出典データセット
uspto-grants-2009_03
特許番号
US07501410B2

反応ノート

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