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

HRID 1788528노트

반응식

HRID 1788528 반응식
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

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 887Methanol용매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-8b66773aa0bf407c865d37bd2c2576a1
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07511145B2

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