Water → HCID 178461233、化合物

HRID 81275ノート

反応式

HRID 81275 の反応式
Cl[C:2]1[C:7]2[N:8]([CH2:20][C@H:21]3[CH2:26][CH2:25][C@H:24]([CH3:27])[CH2:23][CH2:22]3)[C:9]([N:11]3[CH2:16][CH2:15][O:14][C@@H:13]4[CH2:17][CH2:18][CH2:19][C@@H:12]34)=[N:10][C:6]=2[CH:5]=[C:4]([Cl:28])[N:3]=1.[CH2:29]([O:36][C:37]1[C:42](B(O)O)=[CH:41][C:40]([Cl:46])=[CH:39][N:38]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([O-])([O-])=O.[Na+].[Na+].O>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CCOC(C)=O>[CH2:29]([O:36][C:37]1[C:42]([C:2]2[C:7]3[N:8]([CH2:20][C@H:21]4[CH2:26][CH2:25][C@H:24]([CH3:27])[CH2:23][CH2:22]4)[C:9]([N:11]4[CH2:16][CH2:15][O:14][C@@H:13]5[CH2:17][CH2:18][CH2:19][C@@H:12]45)=[N:10][C:6]=3[CH:5]=[C:4]([Cl:28])[N:3]=2)=[CH:41][C:40]([Cl:46])=[CH:39][N:38]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 53216265(2-(Benzyloxy)-5-chloropyridin-3-yl)boronic acidHCID 178461234HCID 178461234、化合物

生成物 1

HCID 178461233HCID 178461233、化合物

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

4,6-dichloro-2-[(trans)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine (racemic, 460 mg, 1.08 mmol), (2-(benzyloxy)-5-chloropyridin-3-yl)boronic acid (purchased from Combi-Blocks Inc.; 372 mg, 1.41 mmol) and 2M aqueous Na2CO3 (5 mL, 10 mmol) were added to degassed 1,2-dimethoxyethane (15 mL), followed by the addition of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (159 mg, 0.2 mmol). The reaction was heated at 90° C. for 6 hours. Water and EtOAc were added. The aqueous layer was extracted several times with EtOAc. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified on a silica gel column (0 to 30% EtOAc/hexanes) to afford 4-[2-(benzyloxy)-5-chloropyridin-3-yl]-6-chloro-2-[(trans)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine (racemic). MS ES calc'd. for C33H37Cl2N5O2 [M+H]+ 606. found 606.

後処理

  1. customto degassed 1,2-dimethoxyethane (15 mL)
  2. extractionThe aqueous layer was extracted several times with EtOAc
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on a silica gel column (0 to 30% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-acb384fc9b2447aa9505d731daf19ad5
出典データセット
uspto-grants-2014_09
特許番号
US08846657B2

反応ノート

読み込み中…