Sodium Carbonate → HCID 178488738, compound

HRID 2205220Notes

Reaction equation

HRID 2205220 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][C@H:12]3[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14][CH2:13]3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH3:19][O:20][C:21]1[C:26]2[S:27][CH:28]=[CH:29][C:25]=2[C:24](B2OC(C)(C)C(C)(C)O2)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:19][O:20][C:21]1[C:26]2[S:27][CH:28]=[CH:29][C:25]=2[C:24]([C:2]2[N:6]3[N:7]=[C:8]([NH:11][C@H:12]4[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14][CH2:13]4)[CH:9]=[CH:10][C:5]3=[N:4][CH:3]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 90387847HCID 90387847, compoundHCID 178521579HCID 178521579, compound

Product 1

HCID 178488738HCID 178488738, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of trans-4-(3-bromoimidazo[1,2-b]pyridazin-6-ylamino)cyclohexanol (45 mg, 0.145 mmol, 1.0 equiv) in acetonitrile (1.45 mL) was added 2-(7-methoxybenzo[b]thiophen-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (55 mg, 0.188 mmol, 1.3 equiv), bis(triphenylphosphine)palladium(II)dichloride (11 mg, 0.0159 mmol, 0.1 equiv), then sodium carbonate (1.45 mL, 1.0 M aqueous solution, 10 equiv). The reaction mixture was irradiated in the microwave at 150° C. for 10 min. Purification by column chromatography gave 31 mg of the yellow solid, 53%.

Workup

  1. customThe reaction mixture was irradiated in the microwave at 150° C. for 10 min
  2. customPurification by column chromatography

Sources & evidence

ORD record
ord-9b54d4563d5944efaf619ca9ff75d74b
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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