4-Chlorophenylboronic acid → 2-[2-[3-(4-Chlorophenyl)phenyl]-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid

HRID 1788528ノート

反応式

HRID 1788528 の反応式
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:18]4[N:22]([CH:23]5[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]5)[C:21]5[CH:29]=[CH:30][C:31]([C:33]([OH:35])=[O:34])=[CH:32][C:20]=5[N:19]=4)[CH:14]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:36][C:37]1[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.CO.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[CH:17]=[CH:16][C:15]4[C:10](=[CH:11][CH:12]=[C:13]([C:18]5[N:22]([CH:23]6[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]6)[C:21]6[CH:29]=[CH:30][C:31]([C:33]([OH:35])=[O:34])=[CH:32][C:20]=6[N:19]=5)[CH:14]=4)[N:9]=3)[CH:3]=2)=[CH:39][CH:38]=1

参加物

8

反応物 3

HCID 742994-Chlorophenylboronic acidHCID 516892Sodium BicarbonateHCID 52761012-[2-(3-Bromophenyl)-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid

生成物 1

HCID 52761022-[2-[3-(4-Chlorophenyl)phenyl]-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid収率 42.2%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

In dried vial with a Teflon lined screw cap, a solution of Compound 482 (156 mg, 0.31 mmol), 4-chlorophenylboronic acid (73 mg, 0.465 mmol), and Palladium Tetrakis (37 mg, 0.031 mmol) in toluene (9 mL), methanol (2 mL), and saturated sodium bicarbonate in water (900 μL) was degassed, flushed with argon, and sealed. The reaction was stirred for 16 h at 90° C. The completed reaction was then evaporated to dryness, purified via HPLC, and converted to the HCl salt using the standard procedure (as described in Compound 516) to produce the title compound (73 mg, 42% yield).

後処理

  1. customflushed with argon
  2. customsealed
  3. customThe completed reaction
  4. customwas then evaporated to dryness
  5. custompurified via HPLC

出典と根拠

ORDレコード
ord-8b66773aa0bf407c865d37bd2c2576a1
出典データセット
uspto-grants-2009_03
特許番号
US07511145B2

反応ノート

読み込み中…