Sodium borohydride → 1-(1-Methyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine

HRID 75278Notes

Reaction equation

[CH3:1][Mg]Br.[CH3:4][N:5]1[C:13]2[C:8](=[N:9][C:10]([C:20]#[N:21])=[C:11]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH:12]=2)[CH:7]=[CH:6]1.[BH4-].[Na+]>C1COCC1>[CH3:4][N:5]1[C:13]2[C:8](=[N:9][C:10]([CH:20]([NH2:21])[CH3:1])=[C:11]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[CH:12]=2)[CH:7]=[CH:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

Methylmagnesium bromide (3.0 M in THF, 0.60 mL, 1.8 mmol) was added to a stirred solution of 1-methyl-6-morpholino-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile (145 mg, 0.60 mmol) in dry THF (6 mL) at RT. The reaction mixture was stirred for 1 h, then cooled to 0° C. and quenched with MeOH (5 mL). Sodium borohydride (45 mg, 1.2 mmol) was added. The reaction mixture was stirred for 20 minutes, quenched with 1N HCl (1.5 mL), and stirred for an additional 20 minutes. Next, the solution was diluted with saturated aqueous NaHCO3 and extracted with EtOAc (6×). The organic layers were combined, dried over MgSO4, and concentrated to give the title compound as a yellow oil (83%). 1H NMR (500 MHz, CD3OD) δ ppm 7.83 (s, 1H), 7.46 (d, 1H, J=3.5 Hz), 6.56 (d, 1H, J=3.5 Hz), 4.97 (q, 1H, J=7.0 Hz), 3.83-3.90 (m, 4H), 3.84 (s, 3H), 3.01-3.07 (m, 2H), 2.88-2.94 (m, 2H), 1.54 (d, 3H, J=7.0 Hz); ESI-MS m/z [M+H]+ calc'd for C14H20N4O, 261; found 261.

Workup

customquenched with MeOH (5 mL)
stirringThe reaction mixture was stirred for 20 minutes
customquenched with 1N HCl (1.5 mL)
stirringstirred for an additional 20 minutes
additionNext, the solution was diluted with saturated aqueous NaHCO3
extractionextracted with EtOAc (6×)
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-484e3884213d46a9bbffdbedd31a55a2
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835420B2

Reaction notes

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