Potassium Carbonate → Tert-butyl 4-(2-bromothieno[3,2-c]pyridin-4-yl)-1,4-diazepane-1-carboxylate

HRID 549291Notes

Reaction equation

HRID 549291 reaction equation
[Br:1][C:2]1[S:10][C:9]2[CH:8]=[CH:7][N:6]=[C:5](Cl)[C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[N:18]1([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24][CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>CS(C)=O>[Br:1][C:2]1[S:10][C:9]2[CH:8]=[CH:7][N:6]=[C:5]([N:21]3[CH2:22][CH2:23][CH2:24][N:18]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:19][CH2:20]3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 177503902-Bromo-4-chlorothieno(3,2-c)pyridine

Product 1

HCID 67157246Tert-butyl 4-(2-bromothieno[3,2-c]pyridin-4-yl)-1,4-diazepane-1-carboxylateYield 25%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The same procedure above intermediate was used starting from 2-bromo-4-chlorothieno[3,2-c]pyridine (7.5 g, 30.45 mmol), K2CO3 (6.7 g, 33.5 mmol) and tert-butyl 1,4-diazepane-1-carboxylate (21.0 g, 152.2 mmol) in DMSO (30 mL). Purification by flash chromatography 3.04 g of the title compound (Yield 25%). HPLC purity 92%; 1H NMR (270 MHz, CDCl3) δ 1.38 (s, 4.5H), 1.43 (s, 4.5H), 1.96-2.11 (m, 2H), 3.36-3.41 (m, 1H), 3.46-3.51 (m, 1H), 3.65-3.87 (m, 6H), 7.02-7.04 (m, 1H), 7.40-7.42 (m, 1H), 7.94 (d, J=5.4 Hz, 1H). m/z=411.97 (M+H).

Sources & evidence

ORD record
ord-5204429034374800927d088f569b7419
Source dataset
uspto-grants-2011_05
Patent number
US07943639B2

Reaction notes

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