N-[6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl]methanesulfonamide → HCID 46932191, compound

HRID 403688Notes

Reaction equation

HRID 403688 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:14][C:15](=[O:17])[CH3:16])[CH:5]=[C:6]([C:10]([CH3:13])([CH3:12])[CH3:11])[C:7]=1[O:8][CH3:9].CC1(C)C(C)(C)OB([C:26]2[CH:27]=[C:28]3[C:33](=[CH:34][CH:35]=2)[CH:32]=[C:31]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])[CH:30]=[CH:29]3)O1>>[C:10]([C:6]1[CH:5]=[C:4]([NH:14][C:15](=[O:17])[CH3:16])[CH:3]=[C:2]([C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[C:31]([NH:36][S:37]([CH3:40])(=[O:38])=[O:39])[CH:32]=3)[CH:27]=2)[C:7]=1[O:8][CH3:9])([CH3:13])([CH3:12])[CH3:11]

Participants

3

Reactant 2

HCID 49758835N-[6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl]methanesulfonamideHCID 66700053HCID 66700053, compound

Product 1

HCID 46932191HCID 46932191, compound

Conditions

Temperature
90 °C

Procedure

N-(3-bromo-5-tert-butyl-4-methoxyphenyl)acetamide (24 mg, 0.08 mmol) and N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-2-yl)methanesulfonamide (64 mg, 0.18 mmol), were reacted in the same manner as Example 43 Part C, heating in an oil bath at 90° C. for 18 hours to give crude product which was purified on an Isco 4 g silica cartridge eluting with 5% methanol/chloroform to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.39 (s, 9 H), 2.02 (s, 3 H), 3.06 (s, 3 H), 3.16 (s, 3 H), 7.34-7.76 (m, 5 H), 7.84-8.00 (m, 3 H), 9.91 (s, 1 H).

Workup

  1. customto give crude product which
  2. customwas purified on an Isco 4 g silica cartridge
  3. washeluting with 5% methanol/chloroform

Sources & evidence

ORD record
ord-28a7495a65524e0ba247d2b58df0e0de
Source dataset
uspto-grants-2014_06
Patent number
US08748443B2

Reaction notes

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