3-Hydroxybenzaldehyde → 3-{[(3-Chloro-4-fluorophenyl)(2-hydroxy-1-methylethyl)amino]methyl}phenol

HRID 1822174Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH:10]([CH3:13])[CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[F:8].[BH3-]C#N.[Na+].[OH:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=O>ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:22][C:21]2[CH:20]=[C:19]([OH:18])[CH:26]=[CH:25][CH:24]=2)[CH:10]([CH3:13])[CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Conditions

Temperature: 25 °C

Procedure

2-[(3-chloro-4-fluorophenyl)amino]propan-1-ol (1-4, 0.030 g, 0.147 mmol) in DCE (1.0 mL) was treated with NaCNBH3 (0.019 g, 0.295 mmol), and 3-hydroxylbenzaldehyde (0.036 g, 0.295 mmol). The resulting mixture stirred at 25° C. for 24 h then concentrated. The reaction was purified by reverse phase liquid chromotography (Semi-prep YMC C-18 Column 5% CH3CN/H2O up to 95% CH3CN/H2O) to give 3-{[(3-chloro-4-fluorophenyl)(2-hydroxy-1-methylethyl)amino]methyl}phenol (1-5). 1H NMR (300 MHz, CDCl3) δ 7.15 (m, 3H), 6.89 (m, 2H), 6.71 (m, 2H), 4.44 (d, J=10.0 Hz, 2H), 4.00 (m, 1H), 3.73 (s, 2H), 1.19 (d, J=6.7 Hz, 3H). MS 310.3 found, 310.7 (M+H+) required.

Workup

concentrationthen concentrated
customThe reaction was purified by reverse phase liquid chromotography (Semi-prep YMC C-18 Column 5% CH3CN/H2O up to 95% CH3CN/H2O)

Sources & evidence

ORD record: ord-48466df2014f44be8d8a166a21810c29
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07608739B2

Reaction notes

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