Sodium Carbonate → HCID 59384371, compound

HRID 2357078Notes

Reaction equation

HRID 2357078 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:11]([C:24]([F:27])([F:26])[F:25])[CH:10]=2)O1.Br[C:30]1[CH:31]=[CH:32][C:33]([C:36]([NH:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])([C:42]([O:44][CH2:45][CH3:46])=[O:43])[C:37]([O:39][CH2:40][CH3:41])=[O:38])=[N:34][CH:35]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)C.O.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:51]([O:50][C:48]([NH:47][C:36]([C:33]1[CH:32]=[CH:31][C:30]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:11]([C:24]([F:25])([F:26])[F:27])[CH:10]=2)=[CH:35][N:34]=1)([C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:42]([O:44][CH2:45][CH3:46])=[O:43])=[O:49])([CH3:53])([CH3:54])[CH3:52]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 59384288HCID 59384288, compoundHCID 59384382HCID 59384382, compound

Product 1

HCID 59384371HCID 59384371, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

The suspension of 4,4,5,5-tetramethyl-2-(4-(octyloxy)-3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane 3a (136 mg, 0.34 mmol, 1.5 equiv), diethyl 2-(5-bromopyridin-2-yl)-2-(tert-butoxycarbonylamino)malonate (98 mg, 0.23 mmol, 1.0 equiv), Pd(PPh3)4 (26.3 mg, 0.023 mmol, 0.1 equiv), and Na2CO3 (120 mg, 1.14 mmol, 4.0 equiv) in ethanol-H2O was heated at 80° C. for 1 hour. The reaction mixture was filtered and the filtrate was purified by silica gel column to afford the title compound in 77% (110 mg) yield. MS (ESI, M+H+)=625.1; 1H NMR (400 MHz, CDCl3) δ 8.66 (s, 1H), 7.88 (s, 1H), 7.86 (dd, 1H, J=8.4 Hz, J=2.0 Hz), 7.75 (d, J=2.5 Hz), 7.66 (d, 1H, J=8.4 Hz), 7.08 (d, 1H, J=8.4 Hz), 6.82 (s, 1H), 4.30 (m, 4H), 4.09 (t, 2H, J=6.0 Hz), 1.84 (m, 2H), 1.46 (m, 11H), 1.28 (m, 14H), 0.90 (t, 3H, J=7.2 Hz).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was purified by silica gel column

Sources & evidence

ORD record
ord-ca5d22f7408c41398fa255e14cf53af4
Source dataset
uspto-grants-2010_07
Patent number
US07759370B2

Reaction notes

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