Acetaldehyde → 7-Iodo-1-methyl-1,2,3,4-tetrahydro[1]benzofuro[2,3-c]pyridine

Reaction equation

[I:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[CH2:13][CH2:12][NH:11][CH2:10][C:9]=3[O:14][C:4]=2[CH:3]=1.[CH:15](=O)C>>[I:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[CH2:13][CH2:12][NH:11][CH:10]([CH3:15])[C:9]=3[O:14][C:4]=2[CH:3]=1

Participants

Reactant 2

HCID 177Acetaldehyde

HCID 673248767-Iodo-1,2,3,4-tetrahydro[1]benzofuro[2,3-c]pyridine

Product 1

HCID 673233717-Iodo-1-methyl-1,2,3,4-tetrahydro[1]benzofuro[2,3-c]pyridine

Procedure

Synthesized as described for 7-iodo-1,2,3,4-tetrahydro[1]benzofuro[2,3-c]pyridine using acetaldehyde. 1H-NMR (400 MHz, CDCl3): δ 1.60 (d, 3H), 2.92 (m, 2H), 3.37 (m, 1H), 3.59 (m, 1H), 4.77 (m, 1H), 7.46 (d, 1H), 7.64 (dd, 1H), 8.07 (d, 1H), 9.58 (bs, 1H), 10.02 (bs, 1H).

Workup

customSynthesized

Sources & evidence

ORD record: ord-e6d76b0c52b04b57af2a5c5ce776e22f
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765779B2

Reaction notes

Loading…