Potassium Carbonate → tert-Butyl (S)-3-(5-(1-(((benzyloxy)carbonyl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate

HRID 2205610Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[N:23]([CH3:24])[CH:22]=[CH:21][C:5]2=[N:6][C:7]=1[C@@H:8]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:9].CC1(C)C(C)(C)OB([C:33]2[CH2:34][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:36][CH:37]=2)O1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:13]([O:12][C:11]([NH:10][C@H:8]([C:7]1[N:6]=[C:5]2[CH:21]=[CH:22][N:23]([CH3:24])[C:4]2=[CH:3][C:2]=1[C:37]1[CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH:33]=1)[CH3:9])=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of benzyl (S)-(1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate (850 mg, 2.19 mmol), tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate (904 mg, 3.06 mmol), K2CO3 (605 mg, 4.38 mmol) and Pd(dppf)Cl2 (170 mg, 0.22 mmol) in anhydrous DMF (25 mL) was stirred at 100° C. for 5 hours under nitrogen. After the solvent was removed, the residue was purified by silica gel column chromatography (PE/EtOAc=7:1) to give the title compound as a yellow oil (900 mg, 87%). ESI-MS m/z [M+H]+ calc'd for C22H32N4O4, 477. found 477.

Workup

customAfter the solvent was removed
customthe residue was purified by silica gel column chromatography (PE/EtOAc=7:1)

Sources & evidence

ORD record: ord-ff605ea019984e709d141fa17965776b
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371321B2

Reaction notes

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