Potassium Carbonate → 2,2'-(5-(8-(4-(9H-carbazol-9-yl)phenyl)dibenzo[b,d]furan-2-yl)-1,3-phenylene)bis(benzo[d]oxazole)

HRID 1486377ノート

反応式

HRID 1486377 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]3[CH:10]=[CH:11][C:12]([C:14]4[CH:19]=[CH:18][C:17]([N:20]5[C:32]6[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=6[C:26]6[C:21]5=[CH:22][CH:23]=[CH:24][CH:25]=6)=[CH:16][CH:15]=4)=[CH:13][C:7]=3[C:6]=2[CH:33]=1.CC1(C)C(C)(C)OB(C2[CH:43]=[C:44](C3OC4C=CC=CC=4N=3)[CH:45]=[C:46]([C:48]3[O:49][C:50]4[CH:56]=[CH:55][CH:54]=[CH:53][C:51]=4[N:52]=3)[CH:47]=2)O1.C(=O)([O-])[O-].[K+].[K+].O1[CH2:78][CH2:77][O:76][CH2:75][CH2:74]1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH:31]1[C:32]2[N:20]([C:17]3[CH:16]=[CH:15][C:14]([C:12]4[CH:13]=[CH:7][C:8]5[O:9][C:5]6[CH:4]=[CH:3][C:2]([C:44]7[CH:43]=[C:78]([C:77]8[O:76][C:75]9[CH:74]=[CH:14][CH:15]=[CH:16][C:17]=9[N:20]=8)[CH:47]=[C:46]([C:48]8[O:49][C:50]9[CH:56]=[CH:55][CH:54]=[CH:53][C:51]=9[N:52]=8)[CH:45]=7)=[CH:33][C:6]=6[C:10]=5[CH:11]=4)=[CH:19][CH:18]=3)[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:27]=2[CH:28]=[CH:29][CH:30]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 867117283,5-Bis(benzo[d]oxazol-2-yl)phenylboronic Acid Pinacol EsterHCID 1176072539-(4-(8-bromodibenzo[b,d]furan-2-yl)phenyl)-9H-carbazole

生成物 1

HCID 1176072602,2'-(5-(8-(4-(9H-carbazol-9-yl)phenyl)dibenzo[b,d]furan-2-yl)-1,3-phenylene)bis(benzo[d]oxazole)

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A mixture of Compound 13 (1.00 g, 2.28 mmol), 2,2′-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)bis(benzo[d]oxazole) (1.159 g, 2.37 mmol), tetrakis(triphenylphosphine) palladium(0) (0.13 g, 0.11 mmol), potassium carbonate (0.95 g, 6.85 mmol), 1,4-dioxane (20.00 mL), and water (4.00 mL) was degassed with bubbling argon for 20 minutes at 45° C. The reaction was then heated to 100° C. and stirred overnight (16.5 hours), maintaining an argon atmosphere. The precipitated product was filtered, dried, and performed boiling ethyl acetate, chloroform, and methanol washes. The solid product was collected to yield Host-7 (0.75 g, 45%). Confirmed by LCMS (APCI): calculated for C50H29N3O3 (M+H): 720. Found: 720.

後処理

  1. customwas degassed with bubbling argon for 20 minutes at 45° C
  2. temperaturemaintaining an argon atmosphere
  3. filtrationThe precipitated product was filtered
  4. customdried
  5. customThe solid product was collected
  6. customto yield Host-7 (0.75 g, 45%)

出典と根拠

ORDレコード
ord-d5b0144f6583400795a271f0094c36c1
出典データセット
uspto-grants-2016_08
特許番号
US09425408B2

反応ノート

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