Water → HCID 68485937、化合物

HRID 1874887ノート

反応式

HRID 1874887 の反応式
[N:1]([CH2:4][C:5]1[C:6]([F:22])=[C:7]([O:12][C:13]2[CH:14]=[C:15]([CH:18]=[C:19]([Br:21])[CH:20]=2)[C:16]#[N:17])[C:8]([Cl:11])=[CH:9][CH:10]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH2:1][CH2:4][C:5]1[C:6]([F:22])=[C:7]([O:12][C:13]2[CH:14]=[C:15]([CH:18]=[C:19]([Br:21])[CH:20]=2)[C:16]#[N:17])[C:8]([Cl:11])=[CH:9][CH:10]=1

参加物

5

反応物 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 866448903-{[3-(Azidomethyl)-6-chloro-2-fluorophenyl]oxy}-5-bromobenzonitrile

生成物 1

HCID 68485937HCID 68485937、化合物収率 58.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3-{[3-(azidomethyl)-6-chloro-2-fluorophenyl]oxy}-5-bromobenzonitrile (2.04 g, 5.35 mmol) dissolved in THF (30 mL) was treated successively with triphenylphosphine (2.10 g, 8.02 mmol) and water (0.482 g, 26.7 mmol) at 25° C. for 16 h with stirring. The reaction mixture was concentrated to dryness and purified on silica gel (eluted successively with EtOAc (to remove triphylphosphine oxide) followed by a gradient of 100% EtOAc to 10% CH3OH/DCM) to give 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-bromobenzonitrile (1.12 g, 3.15 mmol, 58.9% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.92 (t, 1H), 7.46-7.57 (m, 4H), 3.77 (s, 2H), 1.91 (br. s., 2H). LC-MS (ES+) m/z 354.92, 356.91, 358.88 [M+H].

後処理

  1. concentrationThe reaction mixture was concentrated to dryness
  2. custompurified on silica gel (
  3. washeluted successively with EtOAc (to remove triphylphosphine oxide)

出典と根拠

ORDレコード
ord-8496a06945a8451e9cadcbb995869fa9
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

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