Sodium Carbonate → HCID 68889701, compound

HRID 2218769Notes

Reaction equation

HRID 2218769 reaction equation
Br[CH:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([F:14])[C:8]=2[CH2:7][O:6][C:5]2[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:4]1=2.CC1(C)C(C)(C)OB([C:28]2[CH:37]=[CH:36][C:31]3[NH:32][C:33](=[O:35])[NH:34][C:30]=3[CH:29]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>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.O1CCOCC1>[F:19][C:16]1[CH:17]=[CH:18][C:4]2[C:3](=[CH:2][C:28]3[CH:37]=[CH:36][C:31]4[NH:32][C:33](=[O:35])[NH:34][C:30]=4[CH:29]=3)[C:9]3[CH:10]=[CH:11][CH:12]=[C:13]([F:14])[C:8]=3[CH2:7][O:6][C:5]=2[CH:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 438110655-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-oneHCID 67334734HCID 67334734, compound

Product 1

HCID 68889701HCID 68889701, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Following procedures essentially as described in Example 219, mix 11-bromomethylene-3,7-difluoro-6,11-dihydro-dibenzo[b,e]oxepine (E-isomer, 68 mg, 0.21 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-benzoimidazol-2-one (52 mg, 0.20 mmol), Na2CO3 (2M in water, 251 μL, 0.503 mmol), dioxane (2 mL), and Pd(PPh3)4 (12 mg, 0.010 mmol). Purify on silica gel (12 g) eluting with THF to afford a brown solid. Triturate with acetone to afford 56 mg (74%) of the title compound as a white solid. HPLC (ISO80-10) t=2.42 min, 96%; MS [ES] 375 (M−H); 1H-NMR (DMSO-d6) δ 10.58 (s, 1H), 10.46 (s, 1H), 7.57 (dd, 1H, J=8.8, 7.0 Hz), 7.24 (m, 2H), 7.00 (s, 1H), 6.81 (m, 2H), 6.72 (m, 2H), 6.64 (dd, 1H, J=10.6, 2.6 Hz), 6.59 (s, 1H), 5.55-5.19 (br d, 2H).

Workup

  1. customPurify on silica gel (12 g)
  2. washeluting with THF
  3. customto afford a brown solid
  4. customTriturate with acetone

Sources & evidence

ORD record
ord-81247af6293f4d628ee676f4510d76fe
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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