Methanol → 6-amino-2-(4-bromophenyl)-5-cyclopropyl-N-methyl-2H-indazole-3-carboxamide

HRID 1037526ノート

反応式

HRID 1037526 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]([NH:19][CH3:20])=[O:18])=[C:15]3[C:10]([CH:11]=[C:12]([N+:24]([O-])=O)[C:13]([CH:21]4[CH2:23][CH2:22]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.[Cl-].[NH4+].CO>C(O)C.O.C(Cl)Cl.[Fe]>[NH2:24][C:12]1[C:13]([CH:21]2[CH2:23][CH2:22]2)=[CH:14][C:15]2[C:10]([CH:11]=1)=[N:9][N:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[C:16]=2[C:17]([NH:19][CH3:20])=[O:18]

参加物

8

反応物 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 677763242-(4-bromophenyl)-5-cyclopropyl-N-methyl-6-nitro-2H-indazole-3-carboxamide

生成物 1

HCID 675127246-amino-2-(4-bromophenyl)-5-cyclopropyl-N-methyl-2H-indazole-3-carboxamide収率 69.2%

試薬・触媒・溶媒 4

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

To a suspension of compound (viii) (500 mg, 1.20 mmol) in a mixture of ethanol (30 mL) and water (6 mL) was added ammonium chloride (450 mg, 8.43 mmol) followed by iron powder (470 mg, 8.43 mmol). The mixture was heated to 80° C. and stirred vigorously for 90 min. After cooling to RT, 5% MeOH in DCM solution (50 mL) was added to the reaction mixture. The resulting suspension was filtered through celite and washed with MeOH. The filtrate was concentrated in vacuo to give a yellow solid which was then suspended in water (40 mL) and filtered. The solid was collected and dried to give 6-amino-2-(4-bromophenyl)-5-cyclopropyl-N-methyl-2H-indazole-3-carboxamide (ix) (320 mg, 68%) as a yellow solid. ESI-MS m/z calculated for [M+H]+: 385.07/387.06; found: 385.12/387.10.

後処理

  1. temperatureAfter cooling to RT
  2. filtrationThe resulting suspension was filtered through celite
  3. washwashed with MeOH
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give a yellow solid which
  6. filtrationfiltered
  7. customThe solid was collected
  8. customdried

出典と根拠

ORDレコード
ord-ea654436141d4bbb9aa3ffd62288db25
出典データセット
uspto-grants-2013_10
特許番号
US08546389B2

反応ノート

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