Potassium Carbonate → tert-butyl 7-(tert-butoxycarbonyl(methyl)amino)-5-(3-(ethylsulfonyl)phenyl)-8-methoxy-3-methyl-9H-pyrido[2,3-b]indole-9-carboxylate

HRID 1882283Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]([N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH3:12])[C:8]([O:20][CH3:21])=[C:7]2[C:3]=1[C:4]1[CH:32]=[C:31]([CH3:33])[CH:30]=[N:29][C:5]=1[N:6]2[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].[CH2:34]([S:36]([C:39]1[CH:40]=[C:41](B(O)O)[CH:42]=[CH:43][CH:44]=1)(=[O:38])=[O:37])[CH3:35].O1CCOCC1.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:16]([O:15][C:13]([N:11]([CH3:12])[C:9]1[C:8]([O:20][CH3:21])=[C:7]2[C:3]([C:4]3[CH:32]=[C:31]([CH3:33])[CH:30]=[N:29][C:5]=3[N:6]2[C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])=[C:2]([C:41]2[CH:42]=[CH:43][CH:44]=[C:39]([S:36]([CH2:34][CH3:35])(=[O:37])=[O:38])[CH:40]=2)[CH:10]=1)=[O:14])([CH3:18])([CH3:19])[CH3:17]

Participants

Conditions

Temperature: 140 °C

Procedure

A 5 mL microwave vial was charged with Compound 250 (520 mg, 1.0 mmol), 3-(ethylsulfonyl)phenylboronic acid (321 mg, 1.5 mmol) and Pd(PPh3)4 (116 mg, 0.10 mmol). To the mixture was added dioxane (2 mL) and a saturated aqueous solution of K2CO3 (1 mL). The reaction mixture was heated at 140° C. for 20 min. in microwave. The reaction was diluted with EtOAc and washed with water and brine. The organic extracts were dried (Na2SO4) and concentrated and the crude Compound 251 was taken forward for Boc deprotection.

Workup

washwashed with water and brine
dry with materialThe organic extracts were dried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-8ad3dcad34894d34b16b232b288607f3
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318939B2

Reaction notes

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