Sodium Carbonate → HCID 86638739, compound

HRID 423557Notes

Reaction equation

HRID 423557 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])(=[O:20])=[O:19])=[CH:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.COCCOC>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[CH:17]=[CH:16][C:15]([S:18]([NH:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])(=[O:19])=[O:20])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 7213233tert-Butyl {2-[(4-bromobenzene-1-sulfonyl)amino]ethyl}carbamate

Product 1

HCID 86638739HCID 86638739, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

1,1-Dimethylethyl (2-{[(4′-hydroxy-4-biphenylyl)sulfonyl]amino}ethyl)carbamate (246 mg, 65%) was prepared as an off-white solid from (4-hydroxyphenyl)boronic acid (132 mg, 0.96 mmol), 1,1-dimethylethyl (2-{[(4-bromophenyl)sulfonyl]amino}ethyl)carbamate (362 mg, 0.96 mmol), Pd(PPh3)2Cl2 (100 mg, 0.14 mmol), 2M Na2CO3 (2 mL) and DME (4 mL) in a manner similar to Example 21, Step 3, and worked up in a manner similar to Example 9, Step 3. 1H NMR (400 MHz, DMSO-d6) δ 9.70 (s, 1H), 7.75 (s, 4H), 7.61 (t, 1H, J=5.9 Hz), 7.54 (d, 2H, J=8.6 Hz), 6.84 (d, 2H, J=8.6 Hz), 6.76 (t, 1H, J=5.6 Hz), 2.97-2.89 (m, 2H), 2.76-2.68 (m, 2H), 1.30 (s, 9H); LRMS (ESI), m/z 391 (M−H).

Sources & evidence

ORD record
ord-d3d4e6f922cb40258e893d0e244349b9
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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