Sodium Hydroxide → HCID 58285435, compound

HRID 1942321Notes

Reaction equation

HRID 1942321 reaction equation
[OH-].[Na+].[CH2:3]([NH:10][C:11]1[S:15][C:14]2=[N:16][CH:17]=[C:18](I)[N:13]2[N:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]>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(COC)OC>[CH2:3]([NH:10][C:11]1[S:15][C:14]2=[N:16][CH:17]=[C:18]([C:25]3[CH:24]=[CH:23][C:22]([O:21][CH3:20])=[C:27]([O:28][CH3:29])[CH:26]=3)[N:13]2[N:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 27347023,4-Dimethoxyphenylboronic acidHCID 582853975-Iodo-N-(phenylmethyl)imidazo[2,1-b]-1,3,4-thiadiazol-2-amine

Product 1

HCID 58285435HCID 58285435, compoundYield 52.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

An aqueous solution of NaOH (1.00 ml) was added to a mixture of benzyl-(5-iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-amine (250.00 mg; 0.70 mmol; 1.00 eq.), 3,4-dimethoxyphenylboronic acid (191.59 mg; 1.05 mmol; 1.50 eq.), Pd(PPh3)4 and dimethoxyethane (5.00 ml) under N2. The resulting suspension was heated in the microwave at 90° C. for 30 minutes under N2. The reaction was filtered, washed with dimethoxyethane, water and dried at 40° C. for 18 h. 135.5 mg of the desired product were obtained as a white solid.

Workup

  1. filtrationThe reaction was filtered
  2. washwashed with dimethoxyethane, water
  3. customdried at 40° C. for 18 h

Sources & evidence

ORD record
ord-b372a2b5d27b43b6bfa3946646fde25c
Source dataset
uspto-grants-2013_03
Patent number
US08389554B2

Reaction notes

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