HCID 58545582、化合物 → 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

反応式

HRID 72031 の反応式
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

参加物

5

反応物 2

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

生成物 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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cc8a82c36ca24ed28d14fe7d95d786c2
出典データセット
uspto-grants-2014_09
特許番号
US08822430B2

関連ノート

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