Water → HCID 72203012、化合物

HRID 629063ノート

反応式

HRID 629063 の反応式
I[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[CH3:22])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)=[O:6].[CH3:23][O:24][C:25]1[N:30]=[CH:29][C:28](B(O)O)=[CH:27][N:26]=1.C([O-])([O-])=O.[Na+].[Na+].O>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.COCCOC.CCO>[CH3:23][O:24][C:25]1[N:30]=[CH:29][C:28]([C:2]2[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)=[O:6])=[CH:27][N:26]=1

参加物

8

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27367782-Methoxypyrimidine-5-boronic acidHCID 89907516HCID 89907516、化合物

生成物 1

HCID 72203012HCID 72203012、化合物

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 702Ethanol溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

3-Iodo-4-methyl-N-(4-(trifluoromethoxy)phenyl)benzamide (Stage 13.1, 84 mg, 0.2 mmol), 2-methoxypyrimidin-5-ylboronic acid (61.6 mg, 0.4 mmol), Na2CO3 (63.6 mg, 0.600 mmol), Pd(PPh3)2Cl2 (7.02 mg, 10.00 μmol), water (200 μL), EtOH (133 μL) and DME (1 mL) were added to a vial, which was sealed, evacuated/purged with argon and subjected to MW irradiation at 125° C. for 20 min The RM was diluted with THF (1 mL) and stirred with Si-Thiol (69.4 mg, 0.100 mmol) for a 2 h. The filtrate was evaporated to dryness under reduced pressure to give the crude product which was purified by flash chromatography (Silica gel column, 4 g, DCM/MeOH+1% NH4OH, gradient from 1% to 15% MeOH+1% NH4OH) to afford the title compound as a beige solid. UPLC-MS (Condition 1) tR=2.89 min, m/z=404.1 [M+H]+, m/z=402.2 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.35 (s, 3H) 3.99 (s, 3H) 7.37 (d, J=8.6 Hz, 2H) 7.52 (d, J=8.1 Hz, 1H) 7.88 (d, J=9.3 Hz, 2H), 7.90 (br. s, br. s, 1H) 7.93 (dd, 1H) 8.74 (s, 2H) 10.36 (s, 1H).

後処理

  1. customwas sealed
  2. customevacuated/purged with argon
  3. customsubjected to MW irradiation at 125° C. for 20 min The RM
  4. additionwas diluted with THF (1 mL)
  5. customThe filtrate was evaporated to dryness under reduced pressure
  6. customto give the crude product which
  7. customwas purified by flash chromatography (Silica gel column, 4 g, DCM/MeOH+1% NH4OH, gradient from 1% to 15% MeOH+1% NH4OH)

出典と根拠

ORDレコード
ord-5a14c00021684c09aa26343f44b7aee5
出典データセット
uspto-grants-2016_04
特許番号
US09315489B2

反応ノート

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