Diethyl Ether → 2-(1-Methyl-pyrrolidin-3-ylmethyl)-1H-pyrrolo[2,3-b]pyridine

HRID 2425469Notes

Reaction equation

HRID 2425469 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([CH2:6][C:7]2[NH:15][C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH:8]=2)[CH2:2]1.[CH3:16]COCC>CO.C(N(CC)CC)C>[CH3:16][N:1]1[CH2:5][CH2:4][CH:3]([CH2:6][C:7]2[NH:15][C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH:8]=2)[CH2:2]1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 24758401HCID 24758401, compound

Product 1

HCID 247583992-(1-Methyl-pyrrolidin-3-ylmethyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 22728368Triethylamine methanolSolvent

Procedure

Compound 66 (0.3 g, 1.49 mmol) was converted to compound 67, using the methodology described for compound 9. Yield 0.362 g (80.7%). (TLC ether Rf 0.11), which was used as such to generate the title compound (68) using the methodology as described for compound 28.(Yield 0.17 g, 65%), mp 96-97° C. 1H-NMR (400 MHz, CDCl3): δ N1—H invisible, 8.16 (dd, J=5 Hz, 2 Hz, 1H), 7.77 (dd, J=8 Hz, 2 Hz, 1H), 6.98 (dd, J=8 Hz, 5 Hz, 1H), 6.16 (bs, 1H), 2.92-2.84 (m, 2H), 2.76-2.64 (m, 2H), 2.62-2.50 (m, 2H), 2.34 (s, 3H), 2.40-2.31 (m, 1H), 2.11-2.01 (m, 1H), 1.63-1.53 (m, 1H). (TLC MeOH/triethylamine (97/3) Rf 0.2).

Sources & evidence

ORD record
ord-e54106023e5c4cfc894031a45516d100
Source dataset
uspto-grants-2011_06
Patent number
US07964728B2

Reaction notes

Loading…