Thionyl Chloride → (5-Tert-butyl-2-methoxy-phenyl)-[5-(2,6-diethyl-phenyl)-pyrrolo-[2,3-c]pyridine-1-yl]-methanone

HRID 602562Notes

Reaction equation

S(Cl)(Cl)=O.[C:5]([C:9]1[CH:10]=[CH:11][C:12]([O:18][CH3:19])=[C:13]([CH:17]=1)[C:14]([OH:16])=O)([CH3:8])([CH3:7])[CH3:6].[CH2:20]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH3:29])[C:23]=1[C:30]1[CH:31]=[C:32]2[CH:38]=[CH:37][NH:36][C:33]2=[CH:34][N:35]=1)[CH3:21].C(N(CC)C(C)C)(C)C>C(Cl)Cl.C1COCC1>[C:5]([C:9]1[CH:10]=[CH:11][C:12]([O:18][CH3:19])=[C:13]([C:14]([N:36]2[C:33]3=[CH:34][N:35]=[C:30]([C:23]4[C:22]([CH2:20][CH3:21])=[CH:27][CH:26]=[CH:25][C:24]=4[CH2:28][CH3:29])[CH:31]=[C:32]3[CH:38]=[CH:37]2)=[O:16])[CH:17]=1)([CH3:6])([CH3:7])[CH3:8]

Participants

Conditions

Temperature: 60 °C

Procedure

Thionyl chloride (0.3 mL, excess) is added dropwise to a solution of 5-tert-butyl-2-methoxy-benzoic acid (30 mg, 0.2 mmol) in CH2Cl2 (1 mL) at room temperature. The mixture is heated to 60° C. for 1.5 hours. The solvent is removed to dryness. A solution of 5-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine (10 mg, 0.04 mmol) and N,N-diisopropylethylamine (0.2 mL, excess) in THF (1 mL) is added to the residue. The mixture is stirred at room temperature for 16 hours. The solvent is removed to dryness in vacuo. The crude product is purified by PTLC and eluted with 20% EtOAc in hexane to give 12 mg of (5-tert-butyl-2-methoxy-phenyl)-[5-(2,6-diethyl-phenyl)-pyrrolo-[2,3-c]pyridine-1-yl]-methanone. 1H NMR (CDCl3) 7.56-6.98 (m, 9H), 6.60-6.58 (d, 1H), 3.81 (s, 3H), 2.41-2.24 (q, 4H), 1.31 (s, 9H), 1.08-1.00 (t, 3H).

Workup

customThe solvent is removed to dryness
customThe solvent is removed to dryness in vacuo
customThe crude product is purified by PTLC
washeluted with 20% EtOAc in hexane

Sources & evidence

ORD record: ord-777955bd3f224eeab416135fa2fd8703
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906528B2

Reaction notes

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