Dimethylformamide → 2-Isopropyl-8-(4-phenylpyridin-2-yl)benzofuro[2,3-b]pyridine

HRID 1844924Notes

Reaction equation

HRID 1844924 reaction equation
C([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([C:17]3[C:22]4[O:23][C:24]5[C:29]([C:21]=4[CH:20]=[CH:19][CH:18]=3)=[CH:28][CH:27]=[C:26](C)[N:25]=5)[CH:12]=2)=[CH:7][CH:6]=1)C(C)C.C(O[CH2:34][CH2:35]O)C.[CH3:37]N(C=O)C>>[CH:34]([C:26]1[N:25]=[C:24]2[O:23][C:22]3[C:17]([C:13]4[CH:12]=[C:11]([C:8]5[CH:7]=[CH:6][CH:5]=[CH:10][CH:9]=5)[CH:16]=[CH:15][N:14]=4)=[CH:18][CH:19]=[CH:20][C:21]=3[C:29]2=[CH:28][CH:27]=1)([CH3:35])[CH3:37]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8076Glycol monoethyl etherHCID 901216538-(4-(4-Isobutylphenyl)pyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine

Product 1

HCID 901215622-Isopropyl-8-(4-phenylpyridin-2-yl)benzofuro[2,3-b]pyridineYield 62.6%

Conditions

Temperature
130 °C

Procedure

A mixture of iridium complex (2.3 g, 3.22 mmol), 8-(4-(4-isobutylphenyl)pyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine (2.53 g, 6.44 mmol), 2-ethoxyethanol (60 mL) and DMF (60 mL) was heated at 130° C. overnight. The solvent mixture was evaporated under vacuum. The residue was run through a short silica plug. The reaction mixture was further purified by silica gel column with DCM/heptane as elute to obtain 1.8 g desired product (62.6% yield).

Workup

  1. customThe solvent mixture was evaporated under vacuum
  2. customThe reaction mixture was further purified by silica gel column with DCM/heptane
  3. washas elute

Sources & evidence

ORD record
ord-76187c786d0948719f67a59ce867e6a1
Source dataset
uspto-grants-2015_02
Patent number
US08946697B1

Reaction notes

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