Diphenylmethylidenehydrazine → 4-(N'-benzhydrylidenehydrazino)-2-methyl-N-(2-morpholin-4-yl-ethyl)benzene sulfonamide

HRID 221873ノート

反応式

HRID 221873 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)(=[O:10])=[O:9])=[C:4]([CH3:20])[CH:3]=1.[C:21](=[N:34][NH2:35])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>[C:21](=[N:34][NH:35][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)(=[O:10])=[O:9])=[C:4]([CH3:20])[CH:3]=1)([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

7

反応物 3

HCID 79304DiphenylmethylidenehydrazineHCID 23676156Sodium t-butoxideHCID 595579324-bromo-2-methyl-N-(2-morpholin-4-yl-ethyl)benzene-sulfonamide

生成物 1

HCID 536301814-(N'-benzhydrylidenehydrazino)-2-methyl-N-(2-morpholin-4-yl-ethyl)benzene sulfonamide収率 81%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)触媒HCID 1140Toluene溶媒

反応条件

温度
85 °C

実験手順

To a degassed solution of 4-bromo-2-methyl-N-(2-morpholin-4-yl-ethyl)benzene-sulfonamide (939 mg, 2.58 mmol), benzophenone hydrazone (558 mg, 2.84 mmol, 1.1 eq), and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (75 mg, 0.13 mmol, 0.05 eq) in anhydrous toluene (13 mL, 0.2M) was added sodium tert-butoxide (596 mg, 6.20 mmol, 2.4 eq) followed by palladium(II) acetate (29 mg, 0.13 mmol, 0.05 eq), and the reaction mixture was stirred at 85° C. under nitrogen for 17 h. The reaction mixture was cooled to room temperature and was partitioned between EtOAc and water. The organic layer was washed with water and brine, dried over Na2SO4, and concentrated at reduced pressure. Purification by MPLC (75% EtOAc/hexane) afforded the title compound (1.00 g, 80%) as a white solid. 1H-NMR (DMSO-d6) δ 9.25 (s, 1H), 7.64 to 7.52 (m, 4H), 7.44 to 7.41 (m, 2H), 7.35 to 7.26 (m, 5H), 7.16 to 7.13 (m, 3H), 3.45 (t, J=4.8 Hz, 4H), 2.79 (q, J=6.3 Hz, 2H), 2.47 (s, 3H), 2.21 to 2.15 (m, 6H); MS LC-MS [M+H]+=479, RT=3.15 min.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customwas partitioned between EtOAc and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated at reduced pressure
  6. customPurification by MPLC (75% EtOAc/hexane)

出典と根拠

ORDレコード
ord-fbeeb5d6fadb4240b52012b65a54ad6e
出典データセット
uspto-grants-2012_06
特許番号
US08207166B2

反応ノート

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