HCID 58545582, compound → 2-[5-(6-{2-[pyrrolidin-2-yl]-3H-imidazol-4-yl}-benzo[1,2-b:4,5-b']dithiophene-2-yl)-1H-imidazol-2-yl]-pyrrolidine

HRID 72031

Reaction equation

HRID 72031 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[S:10][C:9]2=[CH:11][C:12]3[CH:16]=[C:15]([Sn](CCCC)(CCCC)CCCC)[S:14][C:13]=3[CH:30]=[C:8]2[CH:7]=1)CCC.C(OC([N:46]1[CH2:50][CH2:49][CH2:48][CH:47]1[C:51]1[N:52](COCC[Si](C)(C)C)[CH:53]=[C:54](Br)[N:55]=1)=O)(C)(C)C>C1(C)C=CC=CC=1.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>[NH:46]1[CH2:50][CH2:49][CH2:48][CH:47]1[C:51]1[NH:55][C:54]([C:15]2[S:14][C:13]3[CH:30]=[C:8]4[CH:7]=[C:6]([C:54]5[NH:55][C:51]([CH:47]6[CH2:48][CH2:49][CH2:50][NH:46]6)=[N:52][CH:53]=5)[S:10][C:9]4=[CH:11][C:12]=3[CH:16]=2)=[CH:53][N:52]=1

Participants

5

Reactant 2

HCID 58545582HCID 58545582, compoundHCID 666201592-[4-Bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 666207262-[5-(6-{2-[pyrrolidin-2-yl]-3H-imidazol-4-yl}-benzo[1,2-b:4,5-b']dithiophene-2-yl)-1H-imidazol-2-yl]-pyrrolidine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Pd(PPh3)4 (61 mg, 0.053 mmol) was added to a degassed solution of 2,6-bis(tri-n-butylstannyl)-benzo[1,2-b:4,5-b′]dithiophene (202 mg, 0.26 mmol) and 2-[4-Bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (260 mg, 0.58 mmol) in toluene (4 mL). The reaction was refluxed for 24 hours, then cooled to room temperature and filtered through CELITE and a palladium scavenging column (Stratospheres™ PL-Guanidine MP SPE+, Part #: PL3514-CM89). The solids were rinsed twice with toluene. The filtrate was concentrated and the crude product purified by flash chromatography to yield the desired, fully protected product (100 mg, 41%). LCMS-ESI+: calculated for C46H68N6O6S2Si2: 920.42; observed [M+1]+: 921.45.

Workup

  1. temperatureThe reaction was refluxed for 24 hours
  2. filtrationfiltered through CELITE
  3. washThe solids were rinsed twice with toluene
  4. concentrationThe filtrate was concentrated
  5. customthe crude product purified by flash chromatography
  6. customto yield the

Sources & evidence

ORD record
ord-cc8a82c36ca24ed28d14fe7d95d786c2
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Linked notes

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