Morpholine → 5-morpholin-4-yl-1H-pyrrolo[2,3-c]pyridine

HRID 966115Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([CH:8]=[CH:9][N:10](C)C)[C:5]([N+]([O-])=O)=[CH:4][N:3]=1.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C([O-])=O.[NH4+]>[Pd].CO.C(Cl)Cl>[N:16]1([C:4]2[CH:5]=[C:6]3[CH:8]=[CH:9][NH:10][C:7]3=[CH:2][N:3]=2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of 450 mg (2 mmol) of [2-(2-chloro-5-nitro-pyridin-4-yl)-vinyl]-dimethyl-amine in a 20 mL of mixed solvent of MeOH—CH2Cl2 (1:1) was treated with 3 mL of morpholine. The reaction mixture was stirred at 65° C. for 8 h. Volatiles were then removed. CH2Cl2 (100 mL) and H2O (30 mL) were added. The organic layer was separated and washed with H2O (30 mL), brine (30 mL), dried over Na2SO4, and concentrated. The red powder was treated with 4.0 g (63 mmol, 32 eq) of ammonium formate and 10% Pd—C (120 mg). The reaction mixture was stirred at 65° C. for 30 min. The reaction mixture was then filtered through a pad of celite and concentrated to obtain a yellow solid. Column chromatography (silica, 5% MeOH/CH2Cl2) provided 210 mg (52% for 2 steps) of 5-morpholin-4-yl-1H-pyrrolo[2,3-c]pyridine as a yellow solid. TLC (silica, 5% MeOH/CH2Cl2): Rf=0.40. MS (electrospray): exact mass calculated for C11H13N3O, 203.11; m/z found, 204.2 [M+H]+.

Workup

customVolatiles were then removed
additionCH2Cl2 (100 mL) and H2O (30 mL) were added
customThe organic layer was separated
washwashed with H2O (30 mL), brine (30 mL)
dry with materialdried over Na2SO4
concentrationconcentrated
stirringThe reaction mixture was stirred at 65° C. for 30 min
filtrationThe reaction mixture was then filtered through a pad of celite
concentrationconcentrated
customto obtain a yellow solid

Sources & evidence

ORD record: ord-d4b66ce51b9c4364b3bcc0e61489b067
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06951851B2

Reaction notes

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